Rustic Overtones started out in the early 1990s as a three-piece cover band known as Aces Wild with Dave Gutter, Jon Roods, and then-drummer and close friend Matthew Esty, playing small bars. This lineup produced the very rare Smile album. The Rustic Overtones gained popularity during the mid to late 1990s in the Portland, Maine, music scene, although it had many self-financed tours throughout the country, mostly the northeastern states. After the release of the band's 1998 album Rooms by the Hour, major record label Arista signed the band spurred on by then-president Clive Davis. The signing lead to "Hardest Way Possible," a song from Rooms By The Hour, which was featured on the soundtrack of the Rob Schneider film The Animal. Arista hired legendary producer Tony Visconti to produce what became the band's 2001 release, ¡Viva Nueva! However, after disagreements with the label, and a shakeup at Arista that saw the band's primary supporter, Clive Davis, depart, the record deal fell through. The band was shortly picked up afterward by Tommy Boy and released the album in 2001, which featured guest appearances by Funkmaster Flex, Imogen Heap, and David Bowie. However, Tommy Boy's deal with Warner Bros. Records ended in 2002, which once again left the band without a record label. The disappointment of two major record deals falling through proved too much for the band members, and they went their separate ways in 2002. Its final performance was a three-hour show at the State Theatre on May 11, 2002.

During the five years that the Rustic Overtones went their separate ways, most of the band members pursued a side-project. Dave Gutter and Jon Roods met up with one-time Overtones drummer Marc Boisvert, and formed Paranoid Social Club, another band that enjoyed success, with its single "Wasted" appearing in the soundtrack to the movie Beerfest. Spencer Albee joined with other local musicians including guitarist Zach Jones, drummer Brian Higgins, and bassist Haché and formed Rocktopus (later "As Fast As" replacing Higgins with drummer Andrew Hodgkins), whose album "Open Letter to the Damned received a 4.5/5 rating from music critic giant Allmusic. Tony McNaboe served as a touring drummer for Ray LaMontagne, and released an R&B solo album in 2003 entitled, "Destination". In addition, saxophonist Ryan Zoidis split his time between Lettuce and Soulive, baritone saxophonist Jason Ward played with several local bands, and trombonist Dave Noyes joined local group Seekonk.

In early spring of 2007, drummer Tony McNaboe took the initiative to begin the process of reuniting the band, calling each former member separately, and telling them that everyone else had already agreed to a reunion.[4] In May 2007, Tony McNaboe, Spencer Albee, and Jon Roods made a surprise announcement on Portland's WCYY that the entire band did indeed plan to reunite, and were in the process of scheduling local reunion shows. On May 29, they announced that they would play two reunion shows at Portland club "The Asylum," one on July 28, 2007 and another on July 29. In addition, after a month of rumors and gossip, the band also announced that they had been working on a new album of previously unreleased material and newly written music, eventually titled Light at the End, which was released independently in late July 2007 coinciding with the two reunion shows.

Although the band originally made it clear that the reunion will only last for the summer, and the members would turn their attention back to their post-Overtones projects after the completion of the two shows and the release of the album, Gutter confirmed in an article for the Portland Press Herald that "reunions will become a regular thing" and that the band is "here to stay."[5] Furthermore, during one of the bands reunion shows, Spencer Albee proclaimed, "we're never going to leave you again, we're sorry".[6] Also, during an interview on a local news station on July 18, 2007 with Gutter and Albee, the two were asked what the future plans are with the band. Gutter responded with "we've got a couple more huge endeavors planned for Rustic Overtones" and Albee stated that "theres no reason to not be together".[7]

On September 8, 2007, the band announced on their MySpace that they were in the process of filming a "feature film documentary," though they did not announce a release date or filming timetable. On November 24, 2007, Spencer Albee announced to the crowd at an Asylum concert that the band would soon re-release the albums Long Division and Light At The End on a national record label to get the albums out to the masses. Two days later, the band announced on their MySpace that the label they had signed with was Velour Music, and hinted that their entire back catalog of albums would soon be released.

On September 17, 2008, the band unexpectedly announced on their Myspace that Spencer Albee, their keyboardist since 1995's Long Division had left the band. Drummer Tony McNaboe explained that Spencer was parting ways on good terms, and that work on a new album would continue as planned with multi-instrumentalist Nigel Hall from Lettuce filling in on keyboards. Hall began to tour as a normal member of the band until he became too busy with other projects to continue as a full-fledged member, still contributing to the recording of the album. On tour the band began to alternate between Hall and Tyler Quist as keyboardists, playing some shows without a keyboardist at all, or having Ryan Zoidis and Dave Noyes take over keyboardist duties on certain songs. The Band continued work on their album in their self-built studio "Limited Productions Limited" throughout 2008 and 2009, and on November 11, 2009, The New Way Out was released.

In the earliest days of the Rustic Overtones, the band was mostly classified as a rock and soul band, citing their heaviest influences as artists such as Earth, Wind, and Fire and Tom Waits, and playing with a raw sound. However, by Rooms by the Hour, the band's sound had become much more refined and diversified, with much more of a jazz influence on songs such as "Pink Belly" and "Machine Maker," and an alternative rock feel on songs such as "The Heist" and "Kicking and Screaming". By the late '90s and into the early 2000s, the band had become heavily influenced by hip-hop music, leading to the heavy production of the entire album, a collaboration with hip-hop veterans Naughty by Nature that appeared on the rap group's 1999 album, and the Viva Nueva! song "Smoke", which when played sometimes featured a guest rapper friend of the band who rapped over an extended outtro to the song. Many believe that this radical switch of style is what contributed to the band's fallout with their Arista record deal, as the company apparently believed that the band's sound on the album would be similar to that of their older material. The album Light at the End sounds most similar to the production and style of Rooms by the Hour, although the album draws from various other phases of the band's musical evolution as well.